Resveratrol and para-coumarate serve as ring precursors for coenzyme Q biosynthesis[S]

• Published in: Journal of lipid research Vol. 56; no. 4; pp. 909 - 919
• Main Authors: Xie, Letian X., Williams, Kevin J., He, Cuiwen H., Weng, Emily, Khong, San, Rose, Tristan E., Kwon, Ohyun, Bensinger, Steven J., Marbois, Beth N., Clarke, Catherine F.
• Format: Journal Article
• Language: English
• Published: United States Elsevier Inc 01.04.2015; The American Society for Biochemistry and Molecular Biology; Elsevier
• Subjects: Animals; antioxidants; Cell Line, Tumor; Coumaric Acids - metabolism; Escherichia coli - metabolism; Humans; isoprenoids; lipids/chemistry; mass spectrometry; Mice; mitochondria; plant polyphenols; Propionates; Resveratrol; Saccharomyces cerevisiae - metabolism; stilbene; Stilbenes - metabolism; ubiquinone; Ubiquinone - biosynthesis; Ubiquinone - chemistry; ubiquinone; plant polyphenols; antioxidants; isoprenoids; lipids/chemistry; mitochondria; stilbene; mass spectrometry
• ISSN: 0022-2275; 1539-7262; 1539-7262
• DOI: 10.1194/jlr.M057919

Coenzyme Q (Q or ubiquinone) is a redox-active polyisoprenylated benzoquinone lipid essential for electron and proton transport in the mitochondrial respiratory chain. The aromatic ring 4-hydroxybenzoic acid (4HB) is commonly depicted as the sole aromatic ring precursor in Q biosynthesis despite the recent finding that para-aminobenzoic acid (pABA) also serves as a ring precursor in Saccharomyces cerevisiae Q biosynthesis. In this study, we employed aromatic 13C6-ring-labeled compounds including 13C6-4HB, 13C6-pABA, 13C6-resveratrol, and 13C6-coumarate to investigate the role of these small molecules as aromatic ring precursors in Q biosynthesis in Escherichia coli, S. cerevisiae, and human and mouse cells. In contrast to S. cerevisiae, neither E. coli nor the mammalian cells tested were able to form 13C6-Q when cultured in the presence of 13C6-pABA. However, E. coli cells treated with 13C6-pABA generated 13C6-ring-labeled forms of 3-octaprenyl-4-aminobenzoic acid, 2-octaprenyl-aniline, and 3-octaprenyl-2-aminophenol, suggesting UbiA, UbiD, UbiX, and UbiI are capable of using pABA or pABA-derived intermediates as substrates. E. coli, S. cerevisiae, and human and mouse cells cultured in the presence of 13C6-resveratrol or 13C6-coumarate were able to synthesize 13C6-Q. Future evaluation of the physiological and pharmacological responses to dietary polyphenols should consider their metabolism to Q.